Hydrazine → HCID 10252560, compound

HRID 1590768Notes

Reaction equation

HRID 1590768 reaction equation
[N:1]([CH2:4][CH2:5][C:6]([C:28]([F:31])([F:30])[F:29])([F:27])[C:7]([F:26])([F:25])[C:8]([F:24])([F:23])[C:9]([F:22])([F:21])[C:10]([F:20])([F:19])[C:11]([F:18])([F:17])[CH2:12][CH2:13][N:14]=[N+]=[N-])=[N+]=[N-].NN>[OH-].[OH-].[Pd+2].CO>[NH2:1][CH2:4][CH2:5][C:6]([C:28]([F:29])([F:30])[F:31])([F:27])[C:7]([F:25])([F:26])[C:8]([F:23])([F:24])[C:9]([F:21])([F:22])[C:10]([F:19])([F:20])[C:11]([F:18])([F:17])[CH2:12][CH2:13][NH2:14]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 10435666HCID 10435666, compound

Product 1

HCID 10252560HCID 10252560, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent3×

Procedure

A mixture of 1,10-diazido-3-trifluoromethyl-3,4,4,5,5,6,6,7,7,8,8-undecafluorodecane (7.2 g, 14.7 mmol), methanol (40 mL), Pearlman's catalyst (0.6 g) and a solution of hydrazine (1.1 g, 36 mmol) in methanol (5 mL) was heated under reflux for 21 hours. The mixture was diluted with methanol and filtered through a pad of celite. Methanol was evaporated and the residue was distilled to give 2.5 g (39%) of 1,10-diamino-3-trifluoromethyl-3,4,4,5,5,6,6,7,7,8,8-undecafluorodecane, a colorless oil; bp 0.2 mm, 85°-95° C./0.2 mm; Glc (OV-17, 110° C. to 260° C. at 16° C./min) RT 5.4 min; IR (neat) 3350, 3050, 2975 and 1050-1380 cm-1 ; 1H NMR (CDCl3) δ 3.0 (t, J=6 Hz, 4H), 2.20 (m, 4H) and 1.23 (s, 4H). Anal Calcd for C11H12F 14 N2 : C, 30.15; H, 2.76; F, 60-70. Found: C, 29.85; H, 2.36; F, 60.32.

Workup

  1. temperatureunder reflux for 21 hours
  2. filtrationfiltered through a pad of celite
  3. customMethanol was evaporated
  4. distillationthe residue was distilled

Sources & evidence

ORD record
ord-0550c06a50ac491ba45bdd5514d873cd
Source dataset
uspto-grants-1993_04
Patent number
US05204441

Reaction notes

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